Introduction to Winning in High Stakes Fantasy Baseball

Hi. My name is Dave McDonald. Some of you may know me from Twitter (@RunDMcD), others by my team name and Twitter display name (Less than Dave), and maybe even some will be familiar with my work in Michael (@SPStreamer) Simione’s Draft Guide where I wrote a very in-depth strategy section. Many of you won’t know me at all yet – and that’s fine too. I’m a high stakes fantasy baseball player – specifically the 5×5 standard rotisserie (roto) game.

How do you define “high stakes” you ask? No one really knows. My friend John Laghezza (@MLBMovingAvg) attempted to find out the answer to this question awhile back.

How do you define a high stakes fantasy league?

— MLB Moving Averages (@MLBMovingAvg) March 13, 2021

The poll was decidedly undecided on the topic. Also, John’s poll didn’t include higher options above a $1,000 entry fee. I know some people would classify high stakes as $2,500+ (which is actually how NFBC defines it as their “high stakes” leagues are $2,500-$15,000 entry fee leagues). So while I don’t exactly know how to define “high stakes,” I can say with certainty that I am a high stakes player.

I started playing high stakes fantasy baseball back in college with CDM games. They had Draft&Play 10 team leagues that you could enter with up to $1,000 entry fees (the winning team won $6,000). After winning some D&Ps for several years, I saw an ad somewhere promoting a $100,000 grand prize in a fantasy baseball game. You could go to 1 of several cities around the US and draft your team in person. It was called the National Fantasy Baseball Championship (or NFBC for short).

The nearest city to me was Chicago where my dad happened to be living at the time – so I went there for my first year. This changed everything for me. I was a poor 23 year-old college student who spent just about every dollar he had to enter that $1,500 contest. Though I came in relatively unprepared (the guy in my league furiously paging through a fantasy baseball magazine after running out of guys to draft 1/3 of the way through was decidedly less prepared than I was) having never done a 15-team or 2 catcher league before, I somehow managed to place 3^rd in my league to get my money back. Regardless of my modest accomplishment, I was hooked.

The next year I went back to Chicago, but this time I brought my boys with me – including the 2019 Auction Overall champion Jake Halusker and my Main Event partner (and successful high stakes player in his own right) Tony DiVincenzo. Those two watched me play NFBC for years before they dipped their toes in though. I was the only idiot willing to spend money he didn’t have because of an obsession. I brought them into fantasy baseball years ago in high school where we became friends, and now I was bringing them into the high stakes world as well. Now the 3 of us (and our other friend Markus who was a more recent addition to our group – “The Consortium” – a few years ago) go to Vegas every year to draft several NFBC high stakes leagues between us.

We help each other in drafts, sometimes we partner together for a league or two (except Jake who doesn’t play well with others), and we talk in a text thread every day throughout the week – especially on Sunday before we set our FAAB. We also have a Google Doc where we update it throughout the week with potential FAAB targets. When you’re playing against some of the best fantasy players in the world, it sure helps to have friends who are also your peers. I may have taught them all initially, but they’re all on my level now – and I can’t think of a better resource than having 3 more sets of eyes that see things at an advanced level as well.

I’ve been playing high stakes fantasy baseball for over 15 years now. I’ve been very successful overall and profitable just about every year – some years more than others, but losing seasons are very rare for me and haven’t happened within recent memory. I tell you this not to boast about my accomplishments, but instead to emphasize that at least some part of my process works – so by sharing that process with you, it might help you in your pursuits of playing high stakes fantasy baseball successfully as well. If the methods that I talk about worked for me, maybe some of them can work for you as well.

To win at the high stakes level, you usually need more than just good player analysis – like knowing which stats and tools to use, implementing different draft and in-season strategies depending on the league, assessing and managing risk, constructing a cohesive roster, etc (I’ll get more in-depth on these topics in future articles). Everyone is so concerned with player analysis, and it is obviously important, but it’s hardly the be-all-end-all when it comes to winning in fantasy baseball. I have won consistently without using advanced player analysis (well, it’s probably fairly advanced compared to some, but there are many of you out there, especially as FanGraphs readers, who go much more in-depth than I do at this stage).

I’m not what you’d call a data scientist. I use tons of data, and I love learning how new stats and research can help me become a better fantasy baseball player, but I don’t enjoy learning the mechanics of baseball just for the fun of it. I want to let people smarter than me run the numbers and come to (hopefully statistically significant) conclusions, and then I’ll figure out if those conclusions can be implemented to help me improve my fantasy baseball game. That’s what I care about. That’s all I care about.

We live in the information age of fantasy baseball now where we have access to pretty much everything we want to know from tons of stats (some might say too many) to batting stance and pitch mix changes. But it wasn’t always this way. Hell, even a few years ago tools like Statcast didn’t exist. Projections were extremely flawed. Twitter wasn’t the bounty of information that it is now.

Back when I started playing, these things didn’t exist at all. Your player analysis was “this guy has hit over .300 the last 4 years – he’s probably going to help me with my team AVG.” Yeah. BABIP wasn’t even a thing back then; and if it was, it wasn’t as prevalent and/or easily accessible as it is today. Trying to analyze players 15 years ago with the tools we had available at the time compared to what we have now would be like comparing Stone Age tools to a Reciprocating Pneumatic Air Saw – which is also apt because much like some of the more advanced statistics out there I don’t know how to use that thing either.

So with player analysis being at such a rudimentary level, it forces you to develop other parts of your game in order to get an edge on your competition. Thus, I learned how to do things like construct a cohesive roster while assessing and managing risks in players and figuring out where the pockets of value were at each position in the draft. As information became more readily available (Twitter is HUGE for this) and stats became more advanced, I became a much better fantasy player. But so did my competition. Now I believe the best fantasy players are those that can combine great strategy with great player analysis. 95% of the articles you read here will help you with the player analysis side of fantasy baseball. I’m going to dive into everything else that can help you be a successful fantasy player – even at the high stakes level.

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My next article will focus on what types of high stakes (and even low stakes) leagues are out there and which ones might be right (or wrong) for you. Everyone is different; we all have different goals, strengths, weaknesses, and lifestyles – all of which come into play. I mentioned playing NFBC here, but I also play Yahoo and Fantrax cash leagues as well. Managing your portfolio is very important. Choosing the correct leagues to play in could be the difference between being profitable and not. My goal is to help you figure out how you can become profitable (or more profitable).